3,4,5-tris(4-chlorophenyl)-4,5-dihydro-1,2,4-oxadiazole | 1419182-30-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,5-tris(4-chlorophenyl)-4,5-dihydro-1,2,4-oxadiazole
• 英文别名: 3,4,5-tris(4-chlorophenyl)-5H-1,2,4-oxadiazole
• CAS: 1419182-30-1
• 化学式: C₂₀H₁₃Cl₃N₂O
• 分子量: 403.695
• InChiKey: TZWTZMUIQXYWPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-chlorobenzaldoxime 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,4,5-tris(4-chlorophenyl)-4,5-dihydro-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis, molecular docking study, and anticancer activity of triaryl-1,2,4-oxadiazole

  摘要：

  This study describes synthesis of a new group of triaryl-1,2,4-oxadiazole derivatives and their anticancer activities. The target compounds were prepared from reaction of different imines and 4-substituted benzohydroxyiminoyl chlorides. All the synthesized compounds were screened for antiproliferative activities against MCF7 and K562 cell lines using MTT assay at 50-mu M concentration. Four compounds that showed more than 50 % cytotoxicity were selected for determination of IC50. Out of these, 6c-1y showed remarkable inhibitory cytotoxicity activity against MCF7 and K562 cell lines with IC50 6.50 and 21.66 mu M, respectively. A molecular modeling study where 6c-1y was docked in the binding site of COX-2 showed a 2.3- hydrogen bond forming via hydroxyl group of Ser516 residue and oxygen of central oxadiazole ring and triaryl moiety of 6c-1y oriented toward the hydrophobic pockets of COX-2. Our data indicate that these derivatives may present promising chemotherapeutic agents, possibly targeting COX-2 pathway.

  DOI：

  10.1007/s00044-012-0436-9

文献信息

• Synthesis, molecular docking study, and anticancer activity of triaryl-1,2,4-oxadiazole
  作者：Parisa Miralinaghi、Mona Salimi、Amirali Amirhamzeh、Mahnaz Norouzi、Hirsa Mostafapour Kandelousi、Abbas Shafiee、Mohsen Amini

  DOI：10.1007/s00044-012-0436-9

  日期：2013.9

  This study describes synthesis of a new group of triaryl-1,2,4-oxadiazole derivatives and their anticancer activities. The target compounds were prepared from reaction of different imines and 4-substituted benzohydroxyiminoyl chlorides. All the synthesized compounds were screened for antiproliferative activities against MCF7 and K562 cell lines using MTT assay at 50-mu M concentration. Four compounds that showed more than 50 % cytotoxicity were selected for determination of IC50. Out of these, 6c-1y showed remarkable inhibitory cytotoxicity activity against MCF7 and K562 cell lines with IC50 6.50 and 21.66 mu M, respectively. A molecular modeling study where 6c-1y was docked in the binding site of COX-2 showed a 2.3- hydrogen bond forming via hydroxyl group of Ser516 residue and oxygen of central oxadiazole ring and triaryl moiety of 6c-1y oriented toward the hydrophobic pockets of COX-2. Our data indicate that these derivatives may present promising chemotherapeutic agents, possibly targeting COX-2 pathway.